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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.2K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.2K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

3.0K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.8K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.8K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Peptide macrocyclization by transition metal catalysis.

Daniel G Rivera1, Gerardo M Ojeda-Carralero1, Leslie Reguera2

  • 1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium. erik.vandereycken@kuleuven.be and Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata y G, Havana 10400, Cuba. dgr@fq.uh.cu.

Chemical Society Reviews
|March 7, 2020
PubMed
Summary
This summary is machine-generated.

Metal-catalyzed reactions offer powerful new ways to create constrained peptide macrocycles for drug discovery. This review covers advances from palladium to 3d metals, enabling diverse peptide structures.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Traditional peptide macrocyclization methods (lactam, lactone, disulfide) introduce conformational constraints.
  • Transition metal catalysis, including ruthenium-catalyzed ring-closing metathesis and copper-catalyzed alkyne-azide cycloaddition, has emerged as a key macrocyclization tool.

Purpose of the Study:

  • To provide a comprehensive overview of metal-catalyzed peptide macrocyclization.
  • To highlight the evolution of methodologies and reactivity modes.
  • To discuss future perspectives and applications in peptide drug discovery.

Main Methods:

  • Review of palladium-catalyzed cross-coupling, C-H activation, heteroatom alkylation/arylation, and annulation processes.
  • Discussion of cycloadditions, alkyne couplings, and 3d metal-catalyzed macrocyclization.
  • Inclusion of decarboxylative radical macrocyclizations and photoredox/transition metal catalysis interplay.

Main Results:

  • Demonstration of the evolution from classic to modern metal-catalyzed approaches for peptide macrocyclization.
  • Emphasis on chemoselectivity and diversity generation in late-stage peptide derivatization.
  • Highlighting recent advancements using 3d metals and novel radical/photoredox strategies.

Conclusions:

  • Metal-catalyzed peptide macrocyclization is a versatile method for generating structurally diverse macrocycles.
  • Diversification of metals, reactivity modes, and tactics offers vast possibilities for peptide functionalization.
  • Encourages further research and applications in chemical biology and peptide drug discovery.